Family-friendly vacation rentals in Watch Hill, Westerly

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Top-rated family-friendly rentals in Watch Hill, Westerly

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favourite

Cottage in Mystic

4.98 out of 5 average rating, 209 reviews

Mystic Cottage Retreat, near downtown

This recently renovated cottage is at the top of a quiet lane with a sweeping meadow view. Single level. Two bedrooms sleep four (queen and two twin beds); new, well-equipped kitchen and one bath, open living area, deck and patio. Light and spacious. Working fireplace, central A/C; W/D; expanded cable TV and wifi; off street parking for two cars. Market/deli nearby; pleasing walk (less than a mile from center of Mystic)- restaurants, shops, marinas, etc. Near Amtrak station. Great retreat!

Mar. 5 – 12

$364 CAD per night

Guest favourite

Guesthouse in Charlestown

4.88 out of 5 average rating, 269 reviews

Cozy All Season Cabin Near Beach at Rockbriar Farm

Small vintage vacation cabin located in Charlestown, RI a 1 mile walk/bike to the town beach. Located on 7 acres called Rockbriar Farm, the cabin is in a wooded setting away from our home affording privacy for guests. One large room includes the futon bed/couch and the one sink; the shower and toilet are in separate room. Cabin also has a cedar enclosed hot water outdoor shower. Clean, cozy but not luxurious! No stove, but coffee maker, microwave, outside grill, and mini fridge.

Sep. 15 – 22

$184 CAD per night

Guest favourite

Home in Stonington

4.95 out of 5 average rating, 166 reviews

Romantic Seaside Cottage in Mystic

This cozy seaside cottage with sleep loft has the look and feel of an old classic yacht inside with modern amenities. Couples will love the water views, screened porch, gas-wood stove, heated stone floor in cedar bathroom, outdoor shower and patio. Another larger 2 bedroom cottage on property is for rent also for families with younger children. This rental is NOT suitable for toddlers or children under 12 due to the open balconies, railings and narrow spiral staircase to the loft.

Dec. 31 – Jan. 7

$370 CAD per night

Guest favourite

Home in Stonington

4.97 out of 5 average rating, 185 reviews

Perfect New England Getaway has a pool/ hot tub

traditional New England style that is not just a great home, but a great vacation compound with lots of amenities and outdoor living spaces. Enjoy recreational activities on land and sea that abound locally. Mystic, Stonington Borough, Westerly, and Watch Hill are all close IMPORTANT INFORMATION: Please be advised Stonington, CT has a STRICT OUTSIDE Noise ordinance after 10pm that is enforced by the Police. If a report is generated for any reason , you will forfeit your deposit.

Jan. 5 – 12

$835 CAD per night

Guest favourite

Farm stay in Hopkinton

4.98 out of 5 average rating, 192 reviews

Farm with a few goats on a lake close to beaches.

This is a bright walk out apartment in our home with a private entrance. We will be here but we give you all the privacy that you want. I have recently lost 3 goats. I still have two goats. This is a rural town 7 miles from Westerly, Rhode Island, and about 12 miles from Mystic. Please read the whole description of this property to make sure it is suitable for your family. Please read my reviews. I think my guests describe the accommodation even better than I do!

Apr. 29 – May 6

$243 CAD per night

Superhost

Home in Greenport

4.94 out of 5 average rating, 136 reviews

Harbor Heights

Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney. My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).

Feb. 26 – Mar. 5

$142 CAD per night

Guest favourite

Guest suite in Westerly

4.96 out of 5 average rating, 120 reviews

Room with a View on Spring Pond

Fab newly decorated suite in 1957 home set on a private pond near Watch Hill, RI. Private entrance with mini kitchen, fridge,microwave, portable induction cooktop,toaster,coffeemaker- every thing but the kitchen sink! Please note: there is no kitchen sink nor oven. Ensuite bath with new towels,robes,linens,and bedding. Outdoor shower ( in addition to an indoor one!) ,grill,lounging area. Near beaches,music,food, Mystic Ct attractions. Great relaxing venue.

Feb. 4 – 11

$388 CAD per night

Guest favourite

Cottage in Charlestown

4.88 out of 5 average rating, 133 reviews

Pet-Friendly Private Beach Oceanfront Cottage A/C

Azure Cottage is traditional cedar shingled cottage directly on the private beach in Charlestown, RI with stunning views of Block Island Sound. With two bedrooms and a large queen loft, the cottage sleeps 6. Doggie guests are welcome for an amazing off-the-leash beach vacation. Handheld showers on stairs make washing sandy feet and paws a breeze. Why wait? Book now to reserve for your best summer vacation ever! Pet fees are $30/day per animal.

Dec. 28 – Jan. 4

$1,065 CAD per night

Guest favourite

Guest suite in Brooklyn

4.92 out of 5 average rating, 153 reviews

Affordable In-Law Apartment in Brooklyn, CT

This is a great in-law style apartment which was fully renovated in 2020. It can be booked for short stays or more lengthy visits to Northeast CT. The apartment is one minute from Scenic route 169 and Route 6. It is 30 minutes to UCONN and ECSU. We are close toThe Pomfret School/Rectory School. It is 35 mins to Mohegan Sun and Foxwoods. My place is rural and peaceful. It is good for couples, solo adventurers, business travelers, and families.

Dec. 23 – 30

$114 CAD per night

Guest favourite

Guest suite in South Kingstown

4.94 out of 5 average rating, 116 reviews

Guest suite on private lake

Scenic lake-front guest suite and access to 2 kayaks. Lake is ideal for swimming, fishing and paddle boarding. Five minutes to the Amtrak station, thirty to Newport, RI and fifteen to RI's best beaches. If you are interested in touring New England, the location is ideal for day trips to Martha's Vineyard, Boston, and NYC. Property sits in the shadow of URI. The suite sleeps up to 2 comfortably, with a queen-sized bed.

Aug. 23 – 30

$220 CAD per night

Guest favourite

Apartment in Providence

4.95 out of 5 average rating, 443 reviews

Sunny, East Side apt!

Our one-bedroom apartment is plenty spacious for two people and a cozy stay for more than two. It's a stone's throw away from Hope Village, where there is plenty of charm, shopping, and great food. We are less than a mile from Brown and RISD. The apartment has its own private entrance. There is no parking on the premises, however, there is plenty of free street parking, very often right in front of the house.

Oct. 9 – 16

$131 CAD per night

Guest favourite

Home in Montauk

4.91 out of 5 average rating, 418 reviews

DITCH PLAINS SURF HOUSE

Beach house on quiet street, 200 yards to Montauk's best surfing beach, Ditch Plains. The house is a simple all white home with 2 decks, BBQ, bikes, kayak, and easy open floorplan. You can hear the ocean all day long on this hidden Montauk street. Easily walk or bike to the beach, where you find waves, food trucks in the summer & miles of sand and ocean heading west to Montauk.

Jan. 5 – 12

$331 CAD per night